Common oncogenic emergent conditions of the esophagus are esophageal fistula with malignancy and peptic ulcer, perforation by a foreign body, and rupture (Boerhaave's syndrome) and bleeding with malignancy. The current standard of palliative therapy for patients with malignant tracheoesophageal fistula is endoscopic replacement using covered self-expandable metallic stents in the esophagus and/or trachea. We successfully treated two patients with esophageal bleeding caused by malignant ulceration. To prevent the formation of an aortoesophageal fistula, a covered self-expandable metallic stent was inserted into the esophagus and aorta. Insertion of covered self-expandable metallic stents in patients with esophageal malignancies significantly improves dysphagia, seals fistulas/perforations and ulcerations, and is associated with acceptable morbidity and mortality rates. Spontaneous esophageal rupture, also known as Boerhaave's syndrome, is a rare condition. Primary repair is appropriate for ruptures diagnosed early. Many are diagnosed late and T-tube drainage may be the simplest way to manage this difficult condition in this situation.